Best bet is a problem with fuel pressure, either a weak pump or a bad pressure regulator. When you start the engine, it injects a pre-determined amount of fuel based on holding the injector open for a pre-determined time. If the pressure is a little low, it won't inject enough fuel, but if you give it a little extra it'll start right up. Once the engine is running, it'll automatically adjust the injector cycle to run at the proper speed and mixture, thereby compensating for the reduced flow rate through the injector. When you first turn on the key, you should hear the fuel pump run until it builds a pre-determined pressure or runs for a pre-determined time (not sure which Chrysler uses). If you cycle the key too soon, it won't run again. There should be a valve or connection on the fuel rail where you can attach a guage to measure fuel pressure. If not, you may have to tee into the supply side (not the return side). There should be a specification for fuel pressure prior to starting. I had a Chevy with a similar problem once, and the fuel pressure was only 5 - 10 lbs low. Turned out to be the fuel pump itself, lots of fun dropping the tank to replace it. Carried a small bottle of gas to prime it with for a while until found a guage & figured out what was going on. Good luck, Keith PS...don't know about Chrysler, but Chevy's have a shrader valve on the fuel rail which is the same size as the shrader valve on an automotive air conditioner (don't remember if its the R-12 or R-134 size, but the meter came with an adapter). A $10 air conditioner pressure guage from a chain auto parts store worked just fine as a diagnostic tool. Before someone sqwacks, I'd never use it on an air conditioner once it had gas in it...
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